Arylsulphonylaminosulphonylphenyl-azo-arylene-azo-phenyl dyestuff

ABSTRACT

Dyestuffs of the formula ##SPC1## 
     In which 
     R 1  represents an aromatic radical, an aliphatic radical with 1-4 C atoms or a dialkylamino radical in which the alkyl groups contain 1-4 C atoms, 
     R 2  represents chlorine, bromine, an alkoxy group or an alkyl group, 
     R 3  and R 4  represent hydrogen, chlorine, bromine, an alkoxy group or an alkyl group, 
     R 5  represents hydrogen, chlorine, bromine, fluorine, a phenyl group, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, 
     R 6  represents hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, 
     R 7  represents an arylsulphonyl radical, 
     B represents a 1,4-phenylene, a 1,4-naphthylene or a tetrahydro-1,4-naphthylene radical and 
     m represents a number from 0 to 2, 
     Are suitable for dyeing synthetic fibre materials, especially polyamide fibre materials.

The present invention relates to new, valuable disazo dyestuffs which in the form of the free acid correspond to the general formula ##SPC2##

And to their preparation and use for dyeing synthetic fibre materials, especially polyamide fibre materials.

In the general formula (I)

R₁ represents an aromatic radical, an aliphatic radical with 1-4 C atoms or a dialkylamino radical in which the alkyl groups contain 1-4 C atoms,

R₂ represents chlorine, bromine, an alkoxy group or an alkyl group,

R₃ and R₄ represent hydrogen, chlorine, bromine, an alkoxy group or an alkyl group,

R₅ represents hydrogen, chlorine, bromine, fluorine, a phenyl group, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms,

R₆ represents hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms,

R₇ represents an arylsulphonyl radical,

B represents a 1,4-phenylene, a 1,4-naphthylene or a tetrahydro-1,4-naphthylene radical and

M REPRESENTS A NUMBER FROM 0 TO 2.

Examples of suitable radicals B are radicals of the formulae ##SPC3##

Wherein

R₃ and R₄ have the abovementioned meaning.

Preferred alkyl groups are those with 1-4 C atoms. The alkyl and alkoxy groups can be substituted further, for example, by halogen, nitrile, hydroxyl or optionally substituted phenyl. Examples of suitable alkyl groups are --CH₃, --C₂ H₅, --C₃ H₇, --C₄ H₉, --C₂ H₄ CN, --CH₂ --C₆ H₅ and CF₃.

Preferred alkoxy groups are those with 1-4 C atoms. Suitable alkoxy groups are, for example, --OCH₃, --OC₂ H₅, --OC₃ H₇, --OC₄ H₉, --OCH₂ CH₂ OH and --OCH₂ C₆ H₅.

Examples of suitable dialkylamino radicals R₁ are dimethylamino, diethylamino and dibutylamino.

Suitable aromatic radicals R₁ are, in particular, phenyl radicals. The phenyl radicals can contain further substituents, for example C₁ -C₄ -alkyl groups, C₁ -C₄ -alkoxy groups, halogen, nitrile, nitro and the like. Phenyl and tolyl are preferred. Further suitable aromatic radicals R₁ are 1- and 2-naphthyl radicals. The aliphatic radicals R₁ are, in particular, alkyl radicals.

Examples of suitable arylsulphonyl radicals are phenylsulphonyl, naphthylsulphonyl or tetrahydronapthylsulphonyl radicals which can optionally be substituted further, for example by halogen, such as chlorine and bromine, or by methyl, ethyl, methoxy or nitro groups.

Examples of preferred arylsulphonyl radicals are phenylsulphonyl, o-, m- and p-tolylsulphonyl and o-, m- and p-chlorophenylsulphonyl.

The disulphimide group of the formula (I) is in the ortho-, meta- or para-position to the azo bridge and the radical OR₇ is in the ortho- or para-position to the azo bridge.

Preferred dyestuffs are those of the formula ##SPC4##

wherein

R₁ ' represents an aromatic radical or an aliphatic radical with 1-4 carbon atoms,

R₂ ' represents chlorine, bromine, a methoxy or ethoxy group or a methyl or ethyl group,

R₃ ' represents hydrogen, chlorine, a methyl or methoxy group or an ethyl or ethoxy group,

R₄ ' represents hydrogen, a methyl or methoxy group or an ethyl or ethoxy group,

R₅ ' and R₆ ' independently of one another represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms,

R₇ ' represents a phenylsulphonyl, o-, m- or p-tolylsulphonyl or o-, m- or p-chlorophenylsulphonyl group and

m represents a number from 0 to 2, as well as those of the formula ##SPC5##

wherein

R₁ ', R₂ ', R₅ ', R₆ ', R₇ ' and m have the abovementioned meaning.

Further preferred dyestuffs are those of the formula ##SPC6##

wherein

R₁ ', R₂ ', R₅ ', R₆ ', R₇ ' and m have the abovementioned meaning.

Particularly valuable dyestuffs are those of the formula ##SPC7##

wherein

R₁ ', R₂ ', R₃ ', R₄ ', R₅ ' and R₆ ' have the abovementioned meaning,

R₇ " represents phenylsulphonyl or p-tolylsulphonyl and

m' represents 0 or 1 especially those of the formula ##SPC8##

wherein

R₂ ', R₃ ', R₄ ', R₅ ', R₆ ', R₇ " and m' have the abovementioned meaning and

R₁ " represents an optionally substituted phenyl radical.

Further particularly valuable dyestuffs are those of the formula ##SPC9##

wherein

R₁ ', R₂ ', R₅ ', R₆ ', R₇ " and m' have the abovementioned meaning, especially those of the formula ##SPC10##

wherein

R₂ ', R₅ ', R₆ ', R₇ " and m' have the abovementioned meaning and

R₁ " represents an optionally substituted phenyl radical.

The dyestuffs of the formula (I) are prepared in a known manner, in which amines of the formula ##SPC11##

wherein

R₁, R₂ and m have the abovementioned meaning are diazotised and reacted with amines of the formula ##EQU1## wherein

R₃, R₄ and B have the abovementioned meaning and

Z represents H, --SO₃ H or --CH₂ SO₃ H, to give monoazo dyestuffs of the formula ##SPC12##

the monoazo dyestuffs thus obtained are diazotised, after splitting off the group Z, where necessary, by alkaline or acid saponification, the diazotised compound is coupled with phenols which couple in the ortho-position or para-position to the OH group, of the formula ##SPC13##

wherein

R₅ and R₆ have the abovementioned meaning and thereafter the disazo dyestuffs of the formula ##SPC14##

are esterified with arylsulphonyl halides, preferably the chlorides.

As examples of suitable disulphimides of the formula (IX) there may be mentioned (3-amino-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-benzenesulphonyl)-methanesulphonamide, (3-amino-benzenesulphonyl)-propanesulphonamide, (3-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-methanesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-butanesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-butanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-methanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-methanesulfphonamide, (3-amino-4-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-methanesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-butanesulphomide, (3-amino-6-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-methanesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-butanesulphonamide, (2-amino-benzenesulphonyl)-benzenesulphonamide, (2-amino-benzenesulphonyl)-p-toluenesulphonamide, (2-amino-benzenesulphonyl)-o-toluenesulphonamide, (2-amino-benzenesulphonyl)-methanesulphonamide, (2-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-methanesulphonamide, (3-amino-4-ethyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-benzenesulphonyl)-methanesulphonamide, (4-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-methanesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-butanesulphonamide, (2-amino-3-chloro-4-methyl-benzenesulphonyl)-benzenesulphonamide, (2-amino-3-chloro- 4-methyl-benzenesulphonyl)-benzenesulphonamide, (2-amino-3-chloro-4-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-chloro-5-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-5-chloro-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-5-chloro-6-methyl-benzenesulphonyl)-methanesulphonamide, (4-amino-5-chloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-chloro-benzenesulphonyl)-methanesulphonamide, (4-amino-5-methyl-benzenesulphonyl)-methanesulphonamide, (4-amino-5-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-benzenesulphonyl)-1-napthylsulphonamide, (4-amino-benzenesulphonyl)-2-naphthylsulphonamide, (3-amino-benzenesulphonyl)-N,N-dimethylaminosulphonamide, (4-amino-benzenesulphonyl)-N,N-diethylaminosulphonamide and (3-amino-benzenesulphonyl)-N,N-dibutylaminosulphonamide.

Examples of suitable middle components of the formula (X) are: aniline, 2-aminotoluene, 3-aminotoluene, 2-amino-ethylbenzene, 3amino-ethylbenzene, 3-chloroaniline, 3-bromoaniline, 2-aminoanisole, 3-aminoanisole, 2-amino-ethoxybenzene, 3-amino-ethoxybenzene, 1-amino-2,3-dimethylbenzene, 1-amino-2,5-dimethylbenzene, 1-amino-3,5-dimethylbenzene, 3-amino-4-methoxy-toluene, 2-amino-4-methoxy-toluene, 2-amino-1,4-dimethoxybenzene, 2-amino-4-ethoxy-toluene, 2-amino-1,4-diethoxybenzene, α-naphthylamine, 5,6,7,8-tetrahydro-napthylamine-(1) and their N-sulphonic acids or their N-ω-methanesulphonic acids.

As examples of suitable end components of the formula (XII) there may be mentioned: phenol, o-cresol, m-cresol, p-cresol, 1-hydroxy-4-ethylbenzene, 1-hydroxy-4-tertiary butylbenzene, 1-hydroxy-2-ethylbenzene, 1-hydroxy-2-isopropylbenzene, 1-hydroxy-2-secondary butylbenzene, 3-hydroxy-1,2-dimethylbenzene, 2-hydroxy-1,4-dimethylbenzene, 4-hydroxy-1,2-dimethylbenzene, 2-hydroxy-1,3-diethylbenzene, 1-hydroxy-2-methoxybenzene, 1-hydroxy-3-methoxybenzene, 1-hydroxy-3-ethoxybenzene, 1-hydroxy-4-butoxybenzene and 1-hydroxy-3-butoxybenzene.

As examples of suitable acylating agents there may be mentioned: benzenesulphonic acid chloride, o-, m- and p-chlorobenzenesulphonic acid chloride, 3,4-dichlorobenzenesulphonic acid chloride, 2,5-dichlorobenzenesulphonic acid chloride, o-, m- and p-toluenesulphonic acid chloride, o-, m- and p-nitrobenzenesulphonic acid chloride, 4-chloro-3-nitrobenzenesulphonic acid chloride, 2-chloro-5-nitrobenzenesulphonic acid chloride, 4-chloro-2-toluenesulphonic acid chloride, 2-chloro-4-toluenesulphonic acid chloride, 1,3-dimethyl-4-benzenesulphonic acid chloride, 1,2,3,4-tetrahydronaphthalene-6-sulphonic acid chloride, 1- and 2-naphthalenesulphonic acid chloride, o-, m- and p-methoxybenzenesulphonic acid chloride, o-, m- and p-ethoxybenzenesulphonic acid chloride and the corresponding arylsulphonic acid bromides.

The diazotisation of the amines of the formula (IX) is carried out according to methods which are themselves known, preferably in aqueous mineral acid solution, using sodium nitrite. The coupling of the diazonium compounds of the amines of the formula (IX) with the coupling components of the formula (X) can be effected according to processes which are in themselves known, for example in a neutral to strongly acid, but preferably in a weakly acid, pH range, in an aqueous or organic-aqueous medium.

The monoazo dyestuffs of the formula (XI) are isolated according to known methods, for example by filtration or by salting out with a salt which is soluble in aqueous solution, for example with NaCl or KCl, followed by filtration. If coupling components of the formula (X) with Z = SO₃ H or --CH₂ --SO₃ H are employed, isolation of the monoazo dyestuffs is frequently only necessary after liberation of the amino group of the coupling component effected by alkaline or acid saponification. An intermediate isolation of the monoazo dyestuffs is however not always necessary -- they can also be diazotised further without being isolated.

The further diazotisation of the aminoazo dyestuffs (XI) with Z = H can be effected, for example, in an acid aqueous dispersion by means of sodium nitrite solution, and the diazotisation temperatures can be between 0° and 30°C. Aminoazo dyestuffs of the formula (XI) with Z = H can furthermore also be diazotised indirectly by preparing an alkaline solution thereof, adding sodium nitrite solution and pouring the mixture into aqueous hydrochloric acid, or adding hydrochloric acid.

The coupling of the diazotised aminoazo dyestuffs (XI) with the end components (XII) to give the disazo dyestuffs (XIII) is also carried out in the usual manner, preferably in an aqueous-alkaline medium. The disazo dyestuffs of the formula (XIII) can be isolated by simply filtering them off, if necessary after addition of sodium chloride. If the dyestuffs are obtained in an impure form, they can be recrystallised in a known manner from hot water, if appropriate with addition of alkali.

The reaction of the disazo dyestuffs (XIII) with the arylsulphonic acid halides to give the dyestuffs (I) is effected in the usual manner, for example in an aqueousalkaline medium.

The more sparingly soluble dyestuffs (I) can be rendered readily water-soluble by mixing them with salts of strong bases and weak acids, for example trisodium phosphate, disodium hydrogen phosphate, sodium tetraborate, sodium metaphosphate, sodium metasilicate or sodium carbonate.

The new dyestuffs of the formula (I) can be isolated, or exist as, or be further used as, the free acid or as alkali metal salts or ammonium salts. Suitable alkali metal salts in which the hydrogen atom of the --NH group is thus replaced by an alkali metal cation, are, for example, the sodium salts, potassium salts or lithium salts.

The new dyestuffs are particularly suitable for dyeing and printing natural and synthetic fibre materials containing amide groups, for example fibre materials of wool, silk and polyamide, such as poly-ε-caprolactum or the reaction product of hexamethylenediamine with adipic acid. The resulting dyeings, particularly on polyamide materials, are distinguished by good fastness properties. The dyestuffs of the formula (I) are employed for dyeing either in the form of the free acid (>NH) or as alkali metal salts or the ammonium salt.

In the examples which follow, parts denote parts by weight and percentages denote percentages by weight.

EXAMPLE 1:

31.2 parts of (3-amino-benzenesulphonyl)-benzenesulphonamide are dissolved in 200 parts of water with addition of 10% strength sodium hydroxide solution and 7.0 parts of sodium nitrite are added. The solution thus obtained is allowed to run into 200 parts of ice/H₂ O and 35 parts of concentrated hydrochloric acid and is diazotised in 0.5 hour at 0°-5°C; the excess of nitrous acid is then removed by means of amidosulphonic acid, the diazonium salt suspension is allowed to run into a solution of 20.5 parts of anilino-methanesulphonic acid and 9 parts of sodium bicarbonate in 100 parts of water at 0°-5°C and the pH is kept at between 5 and 7 by further addition of sodium bicarbonate. After completion of coupling, the product is salted out with sodium chloride, filtered off and washed with saturated sodium chloride solution. The moist dyestuff paste is stirred for 1 hour in 200 parts of 7% strength sodium hydroxide solution at 80°-90°C. After completion of the splitting off of the sulphomethyl group, the dyestuff is precipitated by adding sodium chloride, filtered off and washed with saturated sodium chloride solution.

The aminoazo dyestuff thus obtained is dissolved in 500 parts of water, 7.0 parts of sodium nitrite are added, the dyestuff is diazotised by pouring the mixture into 1,000 parts of water and 30 parts of concentrated hydrochloric acid at 10°-20°C over the course of 30 minutes, and the excess nitrous acid is then destroyed with amidosulphonic acid. The diazonium salt suspension thus obtained is stirred into a solution of 9.5 parts of phenol and 4 parts of sodium hydroxide in 200 parts of water at 10°-20°C and the pH is kept at between 8 and 9 by adding 10% strength sodium hydroxide solution. After completion of coupling, the disazo dyestuff is filtered off and dissolved in 500 ml of water at pH 10 by adding concentrated sodium hydroxide solution, and 18.6 g of benzenesulphonyl chloride are added dropwise at 80°. The pH value is kept at 10-10.5 by simultaneous dropwise addition of concentrated sodium hydroxide solution. The mixture is stirred for a further 30 minutes and the dyestuff which has precipitated is filtered off, washed with sodium chloride solution and dried in vacuo at 50°C. In the form of the free acid, the dyestuff corresponds to the formula ##SPC15##

It dyes polyamide, from a weakly acid or neutral bath, in yellow shades of good fastness properties.

DYEING EXAMPLE

0.1 g of the dyestuff is dissolved in 100 ml of hot water, 5 ml of 10% strength ammonium acetate solution are added and the mixture is diluted to a volume of 500 ml with water. 10 g of polyamide fibres are introduced into the dye bath, the bath is brought to the boil over the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the temperature is maintained at the boil for one hour. The fibre material is then rinsed and dried at 70°-80°C.

If the procedure indicated in the preceding example is followed and the starting components, middle components and end components indicated in the table which follows are used, with benzenesulphonic acid chloride as the acylating agent, further disazo dyestuffs of the general formula (I) are obtained, which dye polyamide in yellow to scarlet shades.

    Example                                                                              Starting component                                                                             Middle component                                                                               End component                            __________________________________________________________________________     2     (3-amino-benzenesulphonyl)-                                                                    aniline        o-cresol                                        benzenesulphonamide                                                      3     "               "              m-cresol                                  4     "               "              p-cresol                                  5     "               3-amino-ethylbenzene                                                                          phenol                                    6     "               "              o-cresol                                  7     "               "              p-cresol                                  8     "               3-amino-4-methoxy-toluene                                                                     phenol                                    9     "               "              o-cresol                                  10    "               "              4-tert.-butylphenol                       11    "               "              m-cresol                                  12    "               "              3-methoxy-phenol                          13    "               "              3-ethoxy-phenol                           14    "               "              2-hydroxy-1,4-dimethylbenzene             15    "               "              3-hydroxy-1,2-dimethylbenzene             16    "               "              p-cresol                                  17    "               3-amino-anizole                                                                               phenol                                    18    "               "              o-cresol                                  19    "               "              p-cresol                                  20    (3-amino-benzenesulphonyl)-                                                                    3-amino-3-anisole                                                                             m-cresol                                        benzenesulphonamide                                                      21    "               "              4-tert.-butylphenol                       22    "               "              3-methoxy-phenol                          23    "               "              2-methoxy-phenol                          24    "               "              2-hydroxy-1,4-dimethylbenzene             25    "               2-amino-toluene                                                                               phenol                                    26    "               "              o-cresol                                  27    "               "              p-cresol                                  28    "               "              4-ethyl-phenol                            29    "               "              4-hydroxy-1,2-dimethylbenzene             30    "               "              3-methoxy-phenyl                          31    "               "              2-isopropyl-phenol                        32    "               "              2-isopropyl-phenol                        33    "               "              2-hydroxy-1,3-diethylbenzene              34    "               2-amino-1,4-dimethoxybenzene                                                                  phenol                                    35    "               "              o-cresol                                  36    "               "              p-cresol                                  37    "               "              4-ethyl-phenol                            38    (3-amino-benzenesulphonyl)-                                                                    2-amino-1,4-dimethoxybenzene                                                                  4-hydroxy-1,2-dimethylbenzene                   benzenesulphonamide                                                      39    "               1-amino-2,5-dimethylbenzene                                                                   phenol                                    40    "               "              m-cresol                                  41    "               "              4-ethyl-phenol                            42    "               "              3-methoxy-phenol                          43    "               "              2-hydroxy-1,4-dimethyl-phenol             44    "               2-amino-4-ethoxy-toluene                                                                      phenol                                    45    "               "              m-cresol                                  46    "               "              p-cresol                                  47    "               "              3-ethoxy-phenol                           48    "               "              2-ethyl-phenol                            49    "               aniline        3-methoxy-phenol                          50    "                 "            1-hydroxy-2-ethylbenzene                  51    "                 "            2-hydroxy-1,3-dimethylbenzene             52    "                 "            2-hydroxy-1,4-dimethylbenzene             53    "               3-amino-toluene                                                                               phenol                                    54    "               "              o-cresol                                  55    "               "              p-cresol                                  56    (3-amino-benzenesulphonyl)-                                                                    3-amino-toluene                                                                               1-hydroxy-4-ethylbenzene                        benzenesulphonamide                                                      57    "               "              1-hydroxy-3-ethoxybenzene                 58    "               "              4-hydroxy-1,2-dimethylbenzene             59    "               2-amino-1,4-diethoxybenzene                                                                   phenol                                    60    "               "              4-ethyl-phenol                            61    "               "              4-tert.-butylphenol                       62    "               α-naphthylamine                                                                         p-cresol                                  63    "               "              o-cresol                                  64    "               "              phenol                                    65    "               "              3-methoxy-phenol                          66    "               "              4-ethyl-phenol                            67    "               "              4-tert.-butylphenol                       68    "               "              2-hydroxy-1,4-dimethylbenzene             69    "               "              2-hydroxy-1,3-diethylbenzene              70    "               5,6,7,8-tetrahydro-                                                                           phenol                                                          naphthylamine-(1)                                        71    "               "              o-cresol                                  72    "               "              p-cresol                                  73    (3-amino-benzenesulphonyl)-                                                                    5,6,7,8-tetrahydro-                                                                           4-ethyl-phenol                                  benzenesulphonamide                                                                            naphthylamine-(1)                                        74    "               "              3-methoxy-phenol                          75    "               3-amino-ethylbenzene                                                                          4-hydroxy-1,2-dimethylbenzene             76    "               "              3-methoxy-phenol                          77    "               "              4-tert.-butylphenol                       78    "               2-amino-ethylbenzene                                                                          phenol                                    79    "               "              p-cresol                                  80    "               "              o-cresol                                  81    "               "              4-ethyl-phenol                            82    "               2-amino-anisole                                                                               phenol                                    83    "               "              o-cresol                                  84    "               "              p-cresol                                  85    "               "              3-methoxy-phenol                          86    "               "              4-butoxy-phenol                           87    "               "              2-isopropyl-phenol                        88    "               3-bromo-aniline                                                                               phenol                                    89    "               "              m-cresol                                  90    "               "              4-ethyl-phenol                            91    (3-amino-benzenesulphonyl)-                                                                    3-amino-ethoxybenzene                                                                         phenol                                          benzenesulphonamide                                                      92    "               "              o-cresol                                  93    "               "              4-tert.-butylphenol                       94    "               "              3-methoxy-phenol                          95    "               "              2-methoxy-phenol                          96    "               3-chloro-aniline                                                                              phenol                                    97    "               "              p-cresol                                  98    "               "              2-secondary butylphenol                   99    "               "              4-ethyl-phenol                            100   "               1-amino-2,3-dimethylbenzene                                                                   phenol                                    101   "               "              m-cresol                                  102   "               "              p-cresol                                  103   "               "              4-ethyl-phenol                            104   "               "              3-hydroxy-1,2-dimethylbenzene             105   "               2-amino-4-methoxy-toluene                                                                     phenol                                    106   "               "              o-cresol                                  107   "               "              4-tert.-butylphenol                       108   "               "              3-methoxy-phenol                          Ex-   Starting component                                                                             Middle component                                                                               End component                                                                              Acylating agent              ample                                                                          __________________________________________________________________________     109   (3-amino-benzenesulphonyl)-                                                                    1-amino-2,3-dimethyl-                                                                          o-cresol    o-toluenesulphonic                 methanesulphonamide                                                                            benzene                     acid chloride                110   (3-amino-benzenesulphonyl)-                                                                    2-amino-4-methoxy-                                                                             phenol      p-toluenesulphonic                 propanesulphonic acid amide                                                                    toluene                     acid chloride                111   (3-amino-benzenesulphonyl)-                                                                    aniline         m-cresol    p-chlorobenzenesulph-              butanesulphonic acid amide                  onic acid chloride           112   (3-amino-benzenesulphonyl)-                                                                    2-amino-ethylbenzene                                                                           4-tert.-butylphenol                                                                        p-toluenesulphonic                 p-toluenesulphonamide                       acid chloride                113   (3-amino-benzenesulphonyl)-                                                                    2-amino-1,4-diethoxy-                                                                          2-hydroxy-1,4-                                                                             benzenesulphonic acid              o-toluenesulphonamide                                                                          benzene         dimethylbenzene                                                                            chloride                     114   (3-amino-4-chlorobenzene-                                                                      3-amino-ethoxybenzene                                                                          phenol      o-chlorobenzenesulph-              sulphonyl)-p-toluene-                       onic acid chloride                 sulphonic acid amide                                                     115   (3-amino-6-methylbenzene-                                                                      1-amino-naphthalene                                                                            3-methoxyphenol                                                                            p-toluenesulphonic                 sulphonyl)-benzene-                         acid chloride                      sulphonamide                                                             116   (3-amino-6-methylbenzene-                                                                      3-amino-toluene phenol      benzenesulphonic acid              sulphonyl)-methane-                         chloride                           sulphonic acid amide                                                     117   (3-amino-4-methylbenzene-                                                                      "               m-cresol    o-toluenesulphonic                 sulphonyl)-o-toluene-                       acid chloride                      sulphonamide                                                             118   (3-amino-4-methoxybenzene-                                                                     2-amino-methoxybenzene                                                                         o-cresol    p-toluenesulphonic                 sulphonyl)-benzene-                         acid chloride                      sulphonamide                                                             119   (3-amino-6-methoxybenzene-                                                                     3-amino-ethoxybenzene                                                                          o-cresol    benzenesulphonic acid              sulphonyl)-o-toluene-                       chloride                           sulphonamide                                                             120   (2-amino-benzenesulphonyl)-                                                                    "               p-cresol    o-toluenesulphonic                 benzenesulphonamide                         acid chloride                121   (2-amino-benzenesulphonyl)-                                                                    3-amino-methoxybenzene                                                                         phenol      "                                  methanesulphonamide                                                      122   (3-amino-6-ethylbenzene-                                                                       3-amino-toluene o-cresol    p-toluenesulphonic                 sulphonyl)-p-toluene-                       acid chloride                      sulphonamide                                                             123   (3-amino-6-ethoxybenzene-                                                                      aniline         m-cresol    m-toluenesulphonic                 sulphonyl)-benzene-                         acid chloride                      phonamide                                                                124   (3-amino-6-chlorobenzene-                                                                      2-amino-4-methoxy-                                                                             4-hydroxy-1,2-                                                                             benzenesulphonic acid              sulphonyl)-o-toluene-                                                                          toluene         dimethylbenzene                                                                            bromide                            sulphonamide                                                             125   (4-amino-benzenesulphonyl)-                                                                    2-amino-1,4-dimethoxy-                                                                         phenol      p-toluenesulphonic                 p-toluenesulphonamide                                                                          benzene                     acid chloride                126   (4-amino-benzenesulphonyl)-                                                                    3-amino-toluene 2-ethylphenol                                                                              o-toluenesulphonic                 o-toluenesulphonamide                       acid chloride                127   (4-amino-benzenesulphonyl)-                                                                    "               phenol      benzenesulphonic acid              butanesulphonamide                          chloride                     128   (3-amino-4-bromobenzene-                                                                       2-amino-methoxybenzene                                                                         o-cresol    "                                  sulphonyl)-benzene-                                                            sulphonamide                                                             129   (3-amino-4-bromobenzene-                                                                       3-amino-methoxybenzene                                                                         p-cresol    p-toluenesulphonic                 sulphonyl)-methane-                         acid chloride                      sulphonamide                                                             130   (2-amino-3-chloro-4-methyl-                                                                    "               m-cresol    benzenesulphonic acid              benzenesulphonyl)-benzene-                  chloride                           sulphonamide                                                             131   (3-amino-4-chloro-5-methyl-                                                                    aniline         o-cresol    benzenesulphonic acid              benzenesulphonyl)-benzene-                  chloride                           phonamide                                                                132   (3-amino-5-chloro-6-methyl-                                                                    3-amino-toluene m-cresol    p-toluenesulphonic                 benzenesulphonyl)-methane-                  acid chloride                      sulphonamide                                                             133   (4-amino-5-chlorobenzene-                                                                      aniline         2-ethylphenol                                                                              "                                  sulphonyl)-benzene-                                                            sulphonamide                                                             134   (4-amino-5-methylbenzene-                                                                      3-amino-methoxybenzene                                                                         p-cresol    p-chlorobenzene-                   sulphonyl)-methane-                         sulphonic acid                                                                 chloride                           sulphonamide                                                             135   (3-amino-4-chlorobenzene-                                                                      aniline         m-cresol    p-toluenesulphonic                 sulphonyl)-6-toluene-                       acid chloride                      sulphonamide                                                             136   (3-amino-4-chlorobenzene-                                                                      3-amino-toluene o-cresol    "                                  sulphonyl)-benzene-                                                            sulphonamide                                                             137   (3-amino-benzenesulphonyl)-                                                                    "               m-cresol    benzenesulphonic acid              1-naphthylsulphonamide                      chloride                     138   (3-amino-benzenesulphonyl)-                                                                    aniline         phenol      o-toluenesulphonic                                                             acid                               2-naphthylsulphonamide                      chloride                     139   (3-amino-benzenesulphonyl)-                                                                    3-amino-methoxybenzene                                                                         o-cresol    p-toluenesulphonic                 N,N-dimethylaminosulphon-                   acid chloride                      amide                                                                    140   (3-amino-4-trifluoromethyl-                                                                    2-amino-methoxybenzene                                                                         phenol      "                                  benzenesulphonyl)-benzene-                                                     sulphonamide                                                             141   (3-amino-4-trifluoromethyl-                                                                    aniline         o-cresol    benzenesulphonic acid              benzenesulphonyl)-p-toluene-                chloride                           sulphonamide                                                             142   (4-amino-benzenesulphonyl)-                                                                    "               o-cresol    benzenesulphonic acid              benzenesulphonamide                         chloride                     143   (3-amino-benzenesulphonyl)-                                                                    α-naphthylamine                                                                          p-cresol    p-toluenesulphonic                 benzenesulphonamide                         acid chloride                144   (3-amino-benzenesulphonyl)-                                                                    2,5-dimethoxyaniline                                                                           phenol      "                                  benzenesulphonamide                                                      145   (3-amino-4-chlorobenzene-                                                                      aniline          "          "                                  sulphonyl)-benzene-                                                            sulphonamide                                                             146   (3-amino-benzenesulphonyl)-                                                                    α-naphthylamine                                                                          o-cresol    o-toluenesulphonic                 benzenesulphonamide                         acid chloride                147   (3-amino-benzenesulphonyl)-                                                                    "               phenol      p-chlorobenzene-                   benzenesulphonamide                         sulphonic acid               __________________________________________________________________________                                                       chloride                 

What is claimed is:
 1. Disazo dyestuff which in the form of the free acid corresponds to the formula ##SPC16##wherein B is 1,4-phenylene, 5,6,7,8-tetrahydro-1,4-naphthylene or 1,4-naphthalene; R₁ is phenyl, 1-naphthyl, 2-naphthyl, C₁ -C₄ -alkyl, di-C₁ -C₄ -alkylamino, or phenyl substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, cyano, or nitro; R₂ is chlorine, bromine, C₁ -C₄ -alkoxy, C₁ -C₄ -alkyl, substituted C₁ -C₄ -alkoxy, or substituted C₁ -C₄ -alkyl wherein the substituent is halogen, cyano, hydroxyl or phenyl; R₃ and R₄ are hydrogen, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, substituted C₁ -C₄ -alkyl, or substituted C₁ -C₄ -alkoxy wherein the substituent is halogen, cyano, hydroxyl or phenyl; R₅ is hydrogen, chlorine, bromine, fluorine, phenyl, C₁ -C₄ -alkyl, or C₁ -C₄ -alkoxy; R₆ is hydrogen, C₁ -C₄ -alkyl, or C₁ -C₄ -alkoxy; R₇ is phenylsulphonyl, naphthylsulfonyl, tetrahydronaphthylsulfonyl or any of these three radicals further substituted on the carbocyclic nucleus by chlorine, bromine, methyl, ethyl, methoxy, or nitro; and m is a number from 0 to
 2. 2. Disazo dyestuff which in the form of the free acid corrresponds to the formula ##SPC17##wherein R₁ ' is phenyl, C₁ -C₄ -alkyl, or phenyl substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, cyano, or nitro; R₂ ' is chlorine, bromine, methoxy, ethoxy, methyl, or ethyl; R₃ ' is hydrogen, chlorine, methyl, methoxy, ethyl, or ethoxy; R₄ ' is hydrogen, methyl, methoxy, ethyl, or ethoxy; R₅ ' and R₆ ' independently of one another, are hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy; and R₇ ' is phenylsulphonyl, o-, m- or p-tolylsulphonyl, or o-, m- or p-chlorophenylsulphonyl; and m is a number from 0 to
 2. 3. Disazo dyestuff which in the form of the free acid corresponds to the formula ##SPC18##wherein R₁ " is phenyl or tolyl; R₂ " is hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, or ethyl; R₃ " is hydrogen, chlorine, methyl, methoxy, ethyl, or ethoxy; R₄ " is hydrogen, methyl, methoxy, ethyl, or ethoxy; R₅ " and R₆ ", independently of one another, are hydrogen, C₁ -C₄ -alkyl, or C₁ -C₄ -alkoxy; and R₇ " is phenylsulphonyl or p-tolylsulphonyl.
 4. Disazo dyestuff which in the form of the free acid corresponds to the formula ##SPC19##wherein B' is 1,4-naphthylene, or 5,6,7,8-tetrahydro-1,4-naphthylene; R₁ ' is phenyl, C₁ -C₄ -alkyl, or phenyl substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, cyano, or nitro; R₂ ' is hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, or ethyl; R₅ ' and R₆ ' independently of one another, are hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy; R₇ ' is phenylsulphonyl, o-, m- or p-tolylsulphonyl, or o-, m- or p-chlorophenylsulphonyl; and m is a number from 0 to
 2. 5. Disazo dyestuff which in the form of the free acid corresponds to the formula ##SPC20##wherein B' is 1,4-naphthylene or a 5,6,7,8-tetrahydro-1,4-naphthylene; R₁ " is phenyl or tolyl; R₂ " is hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, or ethyl; R₅ " and R₆ " independently of one another, are hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy group; and R₇ " is phenylsulphonyl or p-tolylsulphonyl. 